Whether it’s your first visit to Italy or you’re returning for more, creating the Best Italy itineraries means choosing iconic places you want to see and under-the-radar destinations you want to explore.
We’ve crafted five diverse Italian itineraries, ranging from 5- to 10-day trips, covering top cities, idyllic islands, and southern stretches. Got more time? Slow down and extend your stay at various stops or combine multiple itineraries to create the ultimate two-week or even three-week adventure.
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Best Italy Itineraries That Will Make You Want to Pack Your Bags Immediately!
Highlights of Italy
Allow at least 10 days
Distance: 930 km (577 miles)
From the haunting canals of Venice to the vibrant backstreets of Napoli, this classic tour offers a whirlwind introduction to Italy’s greatest hits. As you traverse the iconic boot, you’ll encounter awe-inspiring Roman ruins, stunning Renaissance masterpieces, and baroque piazzas that make your heart skip a beat. Indulge in mouth-watering regional cuisines that will have you singing “Mamma Mia!” with every bite. Whether you’re savoring gelato in Florence or enjoying a sunset over the Amalfi Coast, this journey is a feast for the senses and stands among the Best Italy Itineraries for those seeking an unforgettable adventure!
Day 1-2: Venice
Begin your journey in Venice, famous for its mesmerizing canals, historic mansions, and iconic gondolas. While Piazza San Marco and Palazzo Ducale are must-sees, consider exploring lesser-known gems like Fondazione Querini Stampalia and Peggy Guggenheim Collection. Enjoy local delicacies at Rialto Market or unwind with cicchetti in the bustling Fondamenta dei Ormesini.
- Travel Tip: Take a 1.5-hour train ride from Venice to Bologna.
Day 3: Bologna
Next, immerse yourself in Bologna, Italy’s culinary haven, known for its medieval architecture and vibrant university scene. Explore landmarks like Basilica di San Petronio and the Pinacoteca Nazionale, and relish authentic local dishes in the bustling Quadrilatero district.
- Travel Tip: A short 40-minute train ride takes you to Florence.
Day 4-5: Florence
Florence is a Renaissance masterpiece in itself. Visit the Duomo, admire the artworks at the Uffizi Gallery, and marvel at Michelangelo’s David at the Galleria dell’Accademia. Stroll around Piazza della Signoria and enjoy the city’s lively ambiance.
- Travel Tip: A 1-hour train journey brings you to Pisa.
Day 6: Pisa
Witness the famous Leaning Tower in Pisa’s Piazza dei Miracoli. Alongside the tower, explore the 12th-century Duomo and Battistero. Don’t miss a walk along the medieval city walls for panoramic views.
- Travel Tip: A 3-hour train ride will lead you to Rome.
Day 7-9: Rome
In Rome, dive into ancient history with visits to the Colosseum, Pantheon, and Vatican Museums, home to the Sistine Chapel. Wander the vibrant streets of Trastevere and enjoy Italian street life in Campo de’ Fiori.
- Travel Tip: From Rome, take a fast train (1.25 hours) to Naples.
Day 10: Naples
Wrap up your journey in Naples, where you can visit the Museo Archeologico Nazionale and savor authentic Neapolitan pizza. The best Italy itineraries often end with a spectacular view of Mt. Vesuvius in the distance.
Northern Grandeur: A 6-Day Tour
Distance: 395 km (245 miles)
This itinerary offers a fascinating exploration of Northern Italy, from Milan’s high-fashion streets to the Renaissance towns of Padua. This route, one of the best Italy itineraries, is ideal for those interested in art, architecture, and fine wines.
Day 1: Milan
Start with the iconic Duomo, Leonardo da Vinci’s Last Supper, and designer boutiques of the Quadrilatero d’Oro. Conclude with an aperitivo along the scenic Navigli canals.
- Travel Tip: Drive 2.5 hours to Mantua.
Day 2: Mantua
Mantua dazzles with its Renaissance palaces like Palazzo Ducale and Palazzo Te. Wander through these historical sites before enjoying a local meal.
- Travel Tip: Drive 1 hour to Sirmione.
Day 3: Sirmione
Relax by Lake Garda, visit the 13th-century Rocca Scaligera, and explore Roman ruins at Grotte di Catullo.
- Travel Tip: Drive 45 minutes to Verona.
Day 4: Verona
Explore Verona’s Roman Arena, Museo di Castelvecchio, and Juliet’s balcony. This romantic city is a highlight in any list of the best Italy itineraries.
- Travel Tip: Drive 50 minutes to Vicenza.
Day 5: Vicenza
In Vicenza, admire the architectural genius of Andrea Palladio at La Rotonda and Teatro Olimpico.
- Travel Tip: A 45-minute drive brings you to Padua.
Day 6: Padua
End the tour with a visit to the Cappella degli Scrovegni, known for Giotto’s frescoes, and the historic Basilica di Sant’Antonio.
Your Best Italy Itineraries With A Taste of Central Italy: A 7-Day Exploration
Distance: 243 km (150 miles)
Central Italy is a feast for the senses, with its verdant vineyards, medieval hill towns, and the sparkling Lago Trasimeno. This 7-day itinerary takes you through southern Tuscany and into neighboring Umbria, where Renaissance art and architecture blend harmoniously with the picturesque countryside. As one of the best Italy itineraries, this journey offers a balance of cultural exploration and serene natural beauty, perfect for those looking to delve into the heart of Italy.
Florence: 2 Days
Begin your adventure in Florence, a city that needs no introduction. Florence, the cradle of the Renaissance, is a cultural hub teeming with masterpieces. Spend your time exploring the Galleria degli Uffizi, where Botticelli’s The Birth of Venus and Leonardo da Vinci’s Annunciation await. Don’t miss the Duomo, with its iconic dome designed by Brunelleschi, and be sure to stroll around Piazza della Signoria to soak in the lively street life. Florence is also home to Michelangelo’s David, which stands proudly in the Galleria dell’Accademia. As the day winds down, take a walk along the Arno River, admiring the Ponte Vecchio.
Next stop: Drive 45 minutes from Florence to Chianti.
Chianti: 1 Day
Day three invites you to the Chianti region, synonymous with world-renowned wines and stunning landscapes. Dedicate your day to exploring Chianti Fiorentino, the northernmost of the two Chianti districts, which is a must-see in the best Italy itineraries. Begin in Greve in Chianti, a quaint town known for its vibrant piazza, surrounded by wine bars and gourmet shops. Enjoy wine tastings at local estates, savoring the region’s robust reds. Continue your journey to Panzano in Chianti, where a hearty steak lunch awaits. Wrap up your day at the Castello di Ama, where contemporary art installations beautifully contrast the ancient stone architecture.
Next stop: Drive 1 hour from Chianti to Siena.
Siena: 1 Day
Siena is a quintessential Tuscan gem that should be included in the best Italy itineraries. With its medieval charm preserved through centuries, the city is renowned for its Gothic architecture and the iconic Torre del Mangia, a tall tower that offers panoramic views of the surrounding Tuscan hills. Siena’s Piazza del Campo, one of the most beautiful squares in Italy, often hosts lively events, including the historic Palio horse race. Nearby, the Siena Cathedral (Duomo) stands as a remarkable example of Gothic architecture, featuring an intricate façade and richly adorned interior. Siena’s timeless beauty makes it an essential stop in any of the best Italy itineraries.
Next stop: Drive 1 hour from Siena to Lago Trasimeno.
Lago Trasimeno: 1 Day
After several days of cultural immersion, enjoy a day of relaxation at Lago Trasimeno, Italy’s fourth-largest lake. This tranquil retreat is a highlight of the best Italy itineraries, offering calm waters and scenic shorelines dotted with medieval towns. Explore Castiglione del Lago, a charming lakeside village perched on a promontory. Wander through its narrow alleys, climb to the medieval fortress, and soak in the breathtaking views of the lake. The serene atmosphere, combined with the rustic beauty of Lago Trasimeno, makes it a must-visit on your list of best Italy itineraries.
Next stop: Drive 45 minutes from Lago Trasimeno to Perugia.
Perugia: 1 Day
Perugia, the capital of Umbria, is an energetic city that deserves a place among the best Italy itineraries. Its historic hilltop center is a labyrinth of narrow streets, each lined with historic buildings. Start at Corso Vannucci, a bustling street filled with cafes and shops. Visit the Galleria Nazionale dell’Umbria to admire masterpieces by renowned Umbrian painters. Head to Piazza IV Novembre, home to the Gothic Cattedrale di San Lorenzo and the ornate Fontana Maggiore. The mix of history, art, and youthful vibrancy makes Perugia a must-see stop in the best Italy itineraries.
Next stop: Drive 30 minutes from Perugia to Assisi.
Assisi: 1 Day
End your Central Italy tour in Assisi, a destination often featured in the best Italy itineraries for its spiritual significance and historical importance. This town, best known as the birthplace of St. Francis, Italy’s patron saint, offers a blend of art, architecture, and peaceful ambiance. The Basilica di San Francesco, a UNESCO World Heritage Site, is a key highlight, adorned with frescoes by Giotto that depict the life of St. Francis. Venture into the dimly lit lower basilica to find St. Francis’ tomb, a sacred site for many pilgrims. The cobbled streets, flower-decked balconies, and serene atmosphere make Assisi an unforgettable conclusion to one of the best Italy itineraries.
Explore The South Coast With Best Italy Itineraries: 7 Days of Coastal Bliss
Distance: 110 km (68 miles)
This 7-day itinerary reveals the breathtaking beauty of Southern Italy, from Naples’ vibrant energy to the dreamlike seascapes of the Amalfi Coast. It’s a summer delight that showcases historical ruins, sun-kissed beaches, and charming islands. As one of the best Italy itineraries, this route guarantees an unforgettable coastal experience.
Naples: 2 Days
Start in Naples, a city full of life, history, and passion. Begin with a visit to the Museo Archeologico Nazionale, home to treasures from Pompeii and Herculaneum. Witness the astonishing Cristo velato (Veiled Christ) at the Cappella Sansevero. For lunch, indulge in authentic Neapolitan pizza at Spaccanapoli. Consider a detour to Campi Flegrei, known for its ancient Greek settlements and volcanic landscape, adding an extra layer of exploration to your journey.
Next stop: Take a 35-minute train from Naples to Pompeii.
Pompeii: 1 Day
Pompeii offers an immersive walk through time. The ruins reveal everyday life frozen in time by the eruption of Mt. Vesuvius. Explore the preserved streets, from ancient villas to the grand amphitheater. Highlights include the haunting frescoes and the world’s first “Beware of the Dog” sign at the House of the Tragic Poet.
Next stop: Take a 30-minute train from Pompeii to Sorrento.
Sorrento: 1 Day
Sorrento’s colorful streets and scenic views make it a delightful stop. Spend the day wandering through vibrant markets and artisan shops selling ceramics. Sip locally made limoncello, a lemon liqueur for which the town is famous. Sorrento is the gateway to the Amalfi Coast, offering stunning views of the Bay of Naples.
Next stop: Take a 25-minute boat from Sorrento to Capri.
Capri: 1 Day
Capri is renowned for its luxurious allure and spectacular natural beauty. The Grotta Azzurra (Blue Grotto) is a must-visit, with its magical blue light. Explore Villa Jovis, the Roman Emperor Tiberius’ former residence, and take the chairlift from Anacapri to Monte Solaro, the island’s highest point.
Next stop: Take a 30-minute boat from Capri to Positano.
Positano: 1 Day
Arriving in Positano by sea is a feast for the eyes, with colorful houses cascading down the hillside. Spend your day exploring the charming streets lined with boutiques and cafes. The pebbled beach offers a place to relax, while the nearby Path of the Gods hiking trail promises spectacular views of the Amalfi Coast.
Next stop: Take a 40-minute bus from Positano to Amalfi.
Amalfi: 1 Day
Amalfi, with its stunning cathedral and bustling piazzas, is a fitting finale. Visit the Cattedrale di Sant’Andrea, stroll along the harbor, and sample the local ceramics. For panoramic coastal views, head to Ravello, a hilltop town famous for its gardens.
A Slice of Southeast Sicily: 5 Days of Baroque Beauty
Allow at least 5 days for this captivating journey through Southeast Sicily, a region renowned for its dramatic baroque architecture, ancient ruins, and gourmet delights. Spanning 297 km (185 miles), this itinerary takes you from the black lava streets of Catania to the awe-inspiring Greek temples of Agrigento. As you traverse this scenic route, you’ll encounter honey-hued towns nestled among citrus and olive groves, with limestone cliffs and rocky canyons adding to the visual splendor. This route is a must for anyone following the best Italy itineraries.
Catania: 1 Day
Begin your journey in Catania, a vibrant city sitting at the base of the mighty Mt. Etna. The city’s unique black-and-white baroque architecture, heavily influenced by the volcanic eruptions, makes it an inspiring starting point. Enjoy breakfast at Caffè Prestipino in the bustling Piazza del Duomo, then explore La Pescheria, a lively fish market that offers a glimpse of local life. Don’t miss the stunning Chiesa di San Benedetto, renowned for its ornate interiors, or the rooftop climb at Chiesa di San Giuliano, which offers panoramic views of the city.
For a more adventurous detour, consider a guided hike to Mt. Etna’s summit if weather permits, adding an extra day to your itinerary. Catania’s bold architecture and culinary flair secure its place among the best Italy itineraries.
Next stop: Drive 65 minutes from Catania to Syracuse.
Syracuse: 1 Day
Syracuse, the birthplace of the legendary mathematician Archimedes, was once deemed the most beautiful city of the ancient world. Today, it remains a stunning blend of history and architecture, making it a vital stop on the best Italy itineraries. Start at Piazza del Duomo, where the majestic Duomo stands, built upon the ruins of a Greek temple. Explore the Parco Archeologico della Neapolis, home to a well-preserved 5th-century BCE Greek theater and the intriguing Ear of Dionysius, a cave with fascinating acoustics. The combination of ancient and baroque influences makes Syracuse a highlight of Southeast Sicily.
Next stop: Drive 40 minutes from Syracuse to Noto.
Noto: Half Day
Noto, a baroque gem that rose from the ashes of a devastating earthquake in 1693, is the first of three stunning towns in the Val di Noto. Its beauty is showcased along Corso Vittorio Emanuele, lined with elegant palazzi, churches, and the impressive Cattedrale di San Nicolò. Noto’s golden-hued buildings bask in the soft glow of the early evening sun, creating an enchanting ambiance. Its charm is why this town is featured prominently in the best Italy itineraries for Sicily.
Next stop: Drive 45 minutes from Noto to Modica.
Modica: Half Day
Continue your baroque journey in Modica, a historic town renowned not only for its architecture but also for its unique chocolate-making tradition. Wander the winding streets of Modica Alta to reach the Duomo di San Giorgio, a striking symbol of Sicilian baroque. Experience the town’s sweet side with a visit to Antica Dolceria Bonajuto, where you can sample its famous grainy chocolate. End your time in Modica with a gelato at Caffè Adamo on Corso Umberto I. This delightful combination of history and gastronomy makes Modica a standout in the best Italy itineraries.
Next stop: Drive 25 minutes from Modica to Ragusa.
Ragusa: 1 Day
Ragusa, another jewel in the Val di Noto, is split into two sections: modern Ragusa Superiore and the historic Ragusa Ibla. Fans of the popular TV series Inspector Montalbano will recognize many familiar sights in Ibla, from its narrow alleys to Piazza Duomo, dominated by the impressive Duomo di San Giorgio. The town’s labyrinthine lanes, ancient palazzi, and sunlit squares make it one of the best Italy itineraries for exploring Sicily’s baroque heartland.
Next stop: Drive 2.5 hours from Ragusa to Agrigento.
Agrigento: 1 Day
Conclude your tour in Agrigento, home to one of the most remarkable archaeological sites in the world, the Valley of the Temples. This UNESCO World Heritage Site is the best-preserved collection of ancient Greek temples outside Greece. The highlight is the Tempio della Concordia, a magnificent structure that stands as a testament to the glory of ancient Akragas. Strolling through the sprawling park, surrounded by olive and almond trees, you’ll be immersed in history and natural beauty, making Agrigento a fitting end to one of the best Italy itineraries.
